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Cheap flights from Toronto to Chicago from C$ 159

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Toronto to Chicago departing on 17/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Toronto to Chicago

Cheap round-trip flights

Logo
4:00 p.m. - 11:44 p.m.YYZ-ORD
8h 44m1 stop
Logo
12:53 p.m. - 9:07 p.m.ORD-YYZ
7h 14m1 stop
C$ 271
Find Deal
Mon, 20 Oct - Thu, 23 Oct
Logo
4:00 p.m. - 11:44 p.m.YYZ-ORD
8h 44m1 stop
Logo
12:53 p.m. - 9:07 p.m.ORD-YYZ
7h 14m1 stop
C$ 273
Find Deal
Mon, 20 Oct - Thu, 23 Oct
WestJet Logo
6:00 a.m. - 4:43 p.m.YKF-ORD
11h 43m1 stop
WestJet Logo
2:20 p.m. - 5:28 a.m.ORD-YKF
14h 08m1 stop
C$ 287WestJet
Find Deal
Thu, 23 Oct - Mon, 27 Oct
WestJet Logo
6:00 a.m. - 4:43 p.m.YKF-ORD
11h 43m1 stop
WestJet Logo
2:20 p.m. - 5:28 a.m.ORD-YKF
14h 08m1 stop
C$ 309WestJet
Find Deal
Thu, 23 Oct - Mon, 27 Oct
Porter Airlines Logo
7:50 a.m. - 8:39 a.m.YTZ-MDW
1h 49mdirect
Porter Airlines Logo
9:35 a.m. - 12:17 p.m.MDW-YTZ
1h 42mdirect
C$ 332Porter Airlines
Find Deal
Sat, 18 Oct - Sat, 25 Oct
Porter Airlines Logo
3:35 p.m. - 4:24 p.m.YTZ-MDW
1h 49mdirect
Porter Airlines Logo
9:35 a.m. - 12:17 p.m.MDW-YTZ
1h 42mdirect
C$ 334Porter Airlines
Find Deal
Thu, 16 Oct - Sun, 19 Oct
Air Canada Logo
3:25 p.m. - 8:17 p.m.YTZ-ORD
5h 52m1 stop
Air Canada Logo
8:40 a.m. - 2:45 p.m.ORD-YTZ
5h 05m1 stop
C$ 347Air Canada
Find Deal
Sat, 18 Oct - Sat, 25 Oct
Air Canada Logo
3:25 p.m. - 8:06 p.m.YTZ-ORD
5h 41m1 stop
Air Canada Logo
8:40 a.m. - 4:45 p.m.ORD-YTZ
7h 05m1 stop
C$ 367Air Canada
Find Deal
Sat, 4 Oct - Mon, 6 Oct
Air Transat Logo
7:50 a.m. - 8:39 a.m.YTZ-MDW
1h 49mdirect
Air Transat Logo
9:35 a.m. - 12:17 p.m.MDW-YTZ
1h 42mdirect
C$ 376Air Transat
Find Deal
Mon, 13 Oct - Mon, 20 Oct
Air Transat Logo
7:50 a.m. - 8:39 a.m.YTZ-MDW
1h 49mdirect
Air Transat Logo
5:20 p.m. - 8:02 p.m.MDW-YTZ
1h 42mdirect
C$ 389Air Transat
Find Deal
Sun, 5 Oct - Tue, 7 Oct

Air Canada flights from Toronto to Chicago

Our best Air Canada deals on Toronto to Chicago flight tickets
Air Canada
18 Oct
YTZ3:25 p.m.Toronto Island
5h 52m
1 stop
ORD8:17 p.m.Chicago O'Hare Intl
25 Oct
ORD8:40 a.m.Chicago O'Hare Intl
5h 05m
1 stop
YTZ2:45 p.m.Toronto Island
C$ 347
Find similar
Air Canada
4 Oct
YTZ3:25 p.m.Toronto Island
5h 41m
1 stop
ORD8:06 p.m.Chicago O'Hare Intl
6 Oct
ORD8:40 a.m.Chicago O'Hare Intl
7h 05m
1 stop
YTZ4:45 p.m.Toronto Island
C$ 367
Find similar
Air Canada
4 Oct
YTZ3:25 p.m.Toronto Island
5h 41m
1 stop
ORD8:06 p.m.Chicago O'Hare Intl
6 Oct
ORD8:40 a.m.Chicago O'Hare Intl
7h 05m
1 stop
YTZ4:45 p.m.Toronto Island
C$ 370
Find similar

WestJet flights from Toronto to Chicago

Our best WestJet deals on Toronto to Chicago flight tickets
WestJet
23 Oct
YKF6:00 a.m.Toronto Region of Waterloo Intl
11h 43m
1 stop
ORD4:43 p.m.Chicago O'Hare Intl
27 Oct
ORD2:20 p.m.Chicago O'Hare Intl
14h 08m
1 stop
YKF5:28 a.m.Toronto Region of Waterloo Intl
C$ 287
Find similar
WestJet
23 Oct
YKF6:00 a.m.Toronto Region of Waterloo Intl
11h 43m
1 stop
ORD4:43 p.m.Chicago O'Hare Intl
27 Oct
ORD2:20 p.m.Chicago O'Hare Intl
14h 08m
1 stop
YKF5:28 a.m.Toronto Region of Waterloo Intl
C$ 309
Find similar
WestJet
24 Oct
YKF6:00 a.m.Toronto Region of Waterloo Intl
11h 43m
1 stop
ORD4:43 p.m.Chicago O'Hare Intl
26 Oct
ORD2:20 p.m.Chicago O'Hare Intl
14h 08m
1 stop
YKF5:28 a.m.Toronto Region of Waterloo Intl
C$ 310
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Toronto to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 96,600 searches. Data last updated 15 September 2025.
Use the filters below to find and compare flights from Toronto to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 20/10

4:00 p.m.-11:44 p.m.

1 stop8h 44m

Chicago O'Hare Intl

Thu 23/10

12:53 p.m.-9:07 p.m.

1 stop7h 14m

C$ 271

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 20/10

4:00 p.m.-11:44 p.m.

1 stop8h 44m

Chicago O'Hare Intl

Thu 23/10

12:53 p.m.-9:07 p.m.

1 stop7h 14m

C$ 273

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Thu 23/10

6:00 a.m.-4:43 p.m.

1 stop11h 43m

Chicago O'Hare Intl

Mon 27/10

2:20 p.m.-5:28 a.m.

1 stop14h 08m

C$ 287

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Thu 23/10

6:00 a.m.-4:43 p.m.

1 stop11h 43m

Chicago O'Hare Intl

Mon 27/10

2:20 p.m.-5:28 a.m.

1 stop14h 08m

C$ 309

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 18/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Sat 25/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 332

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 16/10

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

Chicago Midway

Sun 19/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 334

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 18/10

3:25 p.m.-8:17 p.m.

1 stop5h 52m

Chicago O'Hare Intl

Sat 25/10

8:40 a.m.-2:45 p.m.

1 stop5h 05m

C$ 347

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 4/10

3:25 p.m.-8:06 p.m.

1 stop5h 41m

Chicago O'Hare Intl

Mon 6/10

8:40 a.m.-4:45 p.m.

1 stop7h 05m

C$ 367

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 13/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Mon 20/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 376

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 5/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Tue 7/10

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

C$ 389

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Toronto to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Toronto and Chicago?

What is the cheapest month to fly to Chicago?

The month of June is another great option to travel to Chicago, with average flight prices from Toronto averaging around C$ 311.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as C$ 656. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Tuesday because tickets tend to average around C$ 1,172. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

What is the cheapest time of day to depart on your flight to Chicago?

In the evening is the cheapest time of day to fly from Toronto to Chicago when you can find flight prices for as low as C$ 624. Flying to Chicago in the evening is an ideal time because this is during off-peak travel hours. In the afternoon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,165 per ticket.

What is the cheapest Toronto to Chicago flight route?

Fly from Toronto Island to Chicago Midway for the best Toronto - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Toronto when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around C$ 404 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Toronto for as low as C$ 299 on momondo.

What cabin class options are available on Toronto to Chicago flights?

There are 4 cabin classes available to choose from on Toronto to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Toronto to Chicago flights?

No. A direct flight is the cheapest option for a flight between Toronto to Chicago.

How have Toronto to Chicago flight prices changed over time?

As of September 2025, prices for Toronto to Chicago flights are approximately 28% cheaper when compared to flights at the same time last year.

When to book flights from Toronto to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Toronto to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Toronto to Chicago (YTO to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Toronto to Chicago

Best price found

C$ 211

Fastest flight time

1h 49m

Direct flights

Every day

Airports in Chicago

1 airport
The best one-way flight to Chicago from Toronto in the past 72 hours is C$ 211. The best round-trip flight deal from Toronto to Chicago found on momondo in the last 72 hours is C$ 241.
The fastest flight from Toronto to Chicago takes 1h 49m
Direct flights go from Toronto to Chicago every day.
There is 1 airport near Chicago: Chicago Midway (MDW)
Search flight deals

  • How far is Toronto to Chicago by plane?

    Chicago is 700.6 km away from Toronto. Flights usually cover this in 1h 49m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Toronto to Chicago?

    Prices for flights from Toronto to Chicago are updated daily.

  • How many operators does momondo search for flights from Toronto to Chicago?

  • How old do you have to be to fly from Toronto to Chicago?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Toronto to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Toronto to Chicago?

  • What is the most popular airline from Toronto to Chicago?

Best airlines flying from Toronto to Chicago

Compare and see reviews for airlines that fly from Toronto to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Porter AirlinesPriceFrom C$ 196Free CancellationRating
7.9
363 reviews
Search Porter Airlines flights
Air CanadaPriceFrom C$ 264Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights
American AirlinesPriceFrom C$ 268Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom C$ 279Free CancellationRating
7.4
8,929 reviews
Search United Airlines flights
WestJetPriceFrom C$ 383Free CancellationRating
7.2
3,091 reviews
Search WestJet flights

  • Porter Airlines Flights From Toronto to Chicago

    Across 11 Porter Airlines flights from Toronto to Chicago this week, the average price was C$ 223, with the best Porter Airlines deals starting from C$ 142 round-trip. 363 users have rated Porter Airlines on momondo, with an average score of 7.9/10.

  • United Airlines Flights From Toronto to Chicago

    United Airlines is also a popular choice for this route. United Airlines flight deals for Toronto to Chicago start from as low as C$ 202 round-trip, depending on your selected dates, with average United Airlines deals seen on momondo around C$ 302. United Airlines operates 89 flights to Chicago from Toronto in an average week. Users have rated it 7.4/10 across 8,929 reviews.

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Munster
Hammond
Merrillville

Why use momondo?

Why should I use momondo to find a flight deal from Toronto to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Toronto.

Can I find flights from Toronto to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from Toronto on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Toronto to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Toronto.

I’m not ready to book a flight from Toronto to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Toronto to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport